AR053167A1 - PROCESS FOR THE ENANTIOSELECTIVE SYNTHESIS OF INDIVIDUAL ENANTIOMERS OF ARILMETANSULFINILO DERIVATIVES TIOSUSTITUTED BY ASYMMETRICAL OXIDATION - Google Patents
PROCESS FOR THE ENANTIOSELECTIVE SYNTHESIS OF INDIVIDUAL ENANTIOMERS OF ARILMETANSULFINILO DERIVATIVES TIOSUSTITUTED BY ASYMMETRICAL OXIDATIONInfo
- Publication number
- AR053167A1 AR053167A1 ARP060100957A ARP060100957A AR053167A1 AR 053167 A1 AR053167 A1 AR 053167A1 AR P060100957 A ARP060100957 A AR P060100957A AR P060100957 A ARP060100957 A AR P060100957A AR 053167 A1 AR053167 A1 AR 053167A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- groups
- aryl
- optionally substituted
- independently selected
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Psychiatry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Un método para preparar un compuesto de sulfoxido de la formula (1) ya sea como un enantiomero individual o en una forma enantioméricamente enriquecida en donde: U, V y W están seleccionados, de modo independiente, de un enlace, CH2, CR2324, O, S(O)y, NR11, C(=O), CHOH, CHOR14, C=NOR14 o C=NNR12R13; los anillos A, B y C están opcionalmente sustituidos con 1 a 3 grupos seleccionados de H, F, Cl, Br, I, OR22, NR23R24, NHOH, NO2, CN, CF3, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, heterocicloalquilo de 3-7 miembros, fenilo, heteroarilo de 5 o 6 miembros, arilalquilo, C(=O)R22, CO2R22, OC(=O)R22, C(=O)NR23R24, NR21C(=O)R22, NR21CO2R22, OC(=O)NR23R24 y NR21C(=S)R22; el anillo D está opcionalmente sustituido con un grupo seleccionado de alquilo C1-6, fenilo heteroarilo de 5-10 miembros; X es un enlace, O, NR11, OC(R22)2, C(R22)2O, C(R22)2NR21, NR21C(R22)2, C(=O)NR21, NR21C(=O), S(O)2, S(O)2NR22, NR22S(O)2, C(R22)2C(R22)2, CR21=CR21, C:::C; R2 está seleccionado de H, F, Cl, Br, I, OR16, NR17R18, NHOH, NO2, CN, CF3, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, C(=O)R16, CO2R16, OC(=O)R16, C(=O)NR17R18, NR15C(=O)R16, NR15CO2R16, OC(=O)NR17R18 y NR15C(=S)R16; de modo alternativo, dos grupos R2 pueden estar combinados para formar un grupo metilendioxi, etilendioxi o propilendioxi; Ar1 es arilo C6-10 opcionalmente sustituido con 0-5 R3; cicloalquilo C5-10 opcionalmente sustituido con 0-5 R3; grupo heteroarilo C5- 10 opcionalmente sustituido con 0-5 R3; en donde dicho heteroarilo comprende 1, 2 o 3 heteroátomos seleccionados de N, O, S o Se, en donde: R3 está seleccionado de H, F, Cl, Br, I, OR16, OCF3, NR17R18, NHOH, NO2, CN, CF3, CH2OR16, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, heterocicloalquilo de 3-7 miembros, fenilo, heteroarilo de 5 o 6 miembros, arilalquilo C7-10, C(=O)R16, CO2R16, OC(=O)R16, C(=O)NR17R18, NR15C(=O)R16, NR15CO2R16, OC(=O)NR17R18, NR15C(=S)R16 y NR15S(=O)2R16; de modo alternativo, dos grupos R3 pueden estar combinados para formar un grupo metilendioxi, etilendioxi, o propilendioxi; Y es alquileno C1-6; R1 está seleccionado de CN, C(=O)R14, CO2R11, C(=O)NR12R13, C(=O)NR21OR22, C(=NR11)R12R13, OC(=O)R11, OC(=O)NR12R13, NR12R13, NR21NR12R13, NR21C(=O)R14, NR21C(=O)NR12R13, NR21S(O)2R11, NR21S(O)2NR12R13; R11 en cada aparicion está seleccionado, de modo independiente, de H, alquilo C1-6, cicloalquilo C3-7, arilo C6-10, arilalquilo; en donde dichos grupos alquilo, arilo, arilalquilo están opcionalmente sustituidos con 1 a 3 grupos R20; R12 y R13 en cada aparicion están seleccionados cada uno, de modo independiente, de H, alquilo C1-6, arilo C6-10 y NR23R24 o R12 y R13, junto con el átomo de N al que están unidos, forman y un anillo heterocíclico de 3 a 7 miembros; en donde dichos grupos alquilo, arilo y anillo heterocíclico están opcionalmente sustituidos con 1 a 3 grupos R20; R14 en cada aparicion está seleccionado, de modo independiente, de alquilo C1-6, arilo C6-10 y arilalquilo; en donde dichos grupos alquilo, arilo y arilalquilo están opcionalmente sustituidos, R15 en cada aparicion está seleccionado, de modo independiente, de H, alquilo C1-6, R16 en cada aparicion está seleccionado, de modo independiente, de H, alquilo C1-6 y arlo C6-10, en donde dichos grupos alquilo y arilo están opcionalmente sustituidos con 1 a 3 grupos R20; R17 y R18 en cada aparicion están seleccionados, de modo independiente entre sí, de H, alquilo C1-6 y arilo C6-10 o R17 y R18, junto con el N al que están unidos, forman un anillo heterocíclico de 3-7 miembros; en donde dichos grupos alquilo y arilo, y anillo heterocíclico son opcionalmente sustituidos con 1 a 2 grupos oxo; R20 en cada aparicion está seleccionado, de modo independiente, de F, Cl, Br, I, OR22, NR23R24, NHOH, No2, CN, CF3, alquilo C1-6 opcionalmente sustituido con 1 a 3 OH, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, heterocicloalquilo de 3-7 miembros, fenilo sustituido por 0 a 1 OR25, heteroarilo de 5 o6 miembro, arilalquilo, =O, C(=O)R22, CO2R22, OC(=O)R22, C(=O)NR23R24, NR21C(=O)R2, NR21CO2R22, y OC(=O)NR23R24; R21 en cada aparicion está seleccionado, de modo independiente, de H y alquilo C1-6; R22 en cada aparicion está seleccionado, de modo independiente, de H, alquilo C1-6, alquilo C1-6-OH y arilo C6-10; R23 y R24 en cada aparicion son cada uno independientemente seleccionado de H, alquilo C1-6 y arilo C6-10, o R23 y R24, junto con el N al que están unidos, forman un anillo heterocíclico de 3-7 miembros opcionalmente sustituido con 1 a 3grupos oxo; R25 en cada aparicion está seleccionado, de modo independiente de H, F, Cl, Br, alquilo C1-6 y alquiloxi C1-6; x es 1, 2, 3 o 4; y es 0, 1 o 2; que comprende los pasos de: a) poner en contacto un sulfuro proquiral de la formula (2) en donde Ar, Y y R1 son como se definio con anterioridad, con un complejo de ligandos quirales metálicos, una base y un agente oxidante en un solvente orgánico, y opcionalmente b) aislar el sulfoxido obtenido de la formula (1). Dicho método en donde el compuesto de sulfoxido de formula (1) se obtiene con un exceso enantiomérico de al menos 80%, 95% o 99%.Compuesto de sulfoxido de la formula (1) seleccionado de (-) o (+)-2-[2-(4-clorofenil)bencil]sulfinilacetamida; (-) o (+)-2-[([1,1'-bifenil]-2-ilmetil)sulfinil]acetamida; y (-) o (+)-2-[2-(3,4-diclorofenoxi)-bencil]sulfinilacetamida.A method for preparing a sulfoxide compound of the formula (1) either as an individual enantiomer or in an enantiomerically enriched form wherein: U, V and W are independently selected from a bond, CH2, CR2324, O , S (O) and, NR11, C (= O), CHOH, CHOR14, C = NOR14 or C = NNR12R13; rings A, B and C are optionally substituted with 1 to 3 groups selected from H, F, Cl, Br, I, OR22, NR23R24, NHOH, NO2, CN, CF3, C1-6 alkyl, C2-6 alkenyl, alkynyl C2-6, C3-7 cycloalkyl, 3-7 membered heterocycloalkyl, phenyl, 5- or 6-membered heteroaryl, arylalkyl, C (= O) R22, CO2R22, OC (= O) R22, C (= O) NR23R24, NR21C (= O) R22, NR21CO2R22, OC (= O) NR23R24 and NR21C (= S) R22; Ring D is optionally substituted with a group selected from C1-6 alkyl, 5-10 membered heteroaryl phenyl; X is a bond, O, NR11, OC (R22) 2, C (R22) 2O, C (R22) 2NR21, NR21C (R22) 2, C (= O) NR21, NR21C (= O), S (O) 2, S (O) 2NR22, NR22S (O) 2, C (R22) 2C (R22) 2, CR21 = CR21, C ::: C; R2 is selected from H, F, Cl, Br, I, OR16, NR17R18, NHOH, NO2, CN, CF3, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-7 cycloalkyl, C (= O ) R16, CO2R16, OC (= O) R16, C (= O) NR17R18, NR15C (= O) R16, NR15CO2R16, OC (= O) NR17R18 and NR15C (= S) R16; alternatively, two R2 groups may be combined to form a methylenedioxy, ethylenedioxy or propylenedioxy group; Ar1 is C6-10 aryl optionally substituted with 0-5 R3; C5-10 cycloalkyl optionally substituted with 0-5 R3; C5-10 heteroaryl group optionally substituted with 0-5 R3; wherein said heteroaryl comprises 1, 2 or 3 heteroatoms selected from N, O, S or Se, wherein: R3 is selected from H, F, Cl, Br, I, OR16, OCF3, NR17R18, NHOH, NO2, CN, CF3, CH2OR16, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-7 cycloalkyl, 3-7 membered heterocycloalkyl, phenyl, 5 or 6 membered heteroaryl, C7-10 arylalkyl, C (= O) R16, CO2R16, OC (= O) R16, C (= O) NR17R18, NR15C (= O) R16, NR15CO2R16, OC (= O) NR17R18, NR15C (= S) R16 and NR15S (= O) 2R16; alternatively, two R3 groups may be combined to form a methylenedioxy, ethylenedioxy, or propylenedioxy group; Y is C1-6 alkylene; R1 is selected from CN, C (= O) R14, CO2R11, C (= O) NR12R13, C (= O) NR21OR22, C (= NR11) R12R13, OC (= O) R11, OC (= O) NR12R13, NR12R13, NR21NR12R13, NR21C (= O) R14, NR21C (= O) NR12R13, NR21S (O) 2R11, NR21S (O) 2NR12R13; R11 in each occurrence is independently selected from H, C1-6 alkyl, C3-7 cycloalkyl, C6-10 aryl, arylalkyl; wherein said alkyl, aryl, arylalkyl groups are optionally substituted with 1 to 3 R20 groups; R12 and R13 in each occurrence are each independently selected from H, C1-6 alkyl, C6-10 aryl and NR23R24 or R12 and R13, together with the N atom to which they are attached, form and a heterocyclic ring from 3 to 7 members; wherein said alkyl, aryl and heterocyclic ring groups are optionally substituted with 1 to 3 R20 groups; R14 in each occurrence is independently selected from C1-6 alkyl, C6-10 aryl and arylalkyl; wherein said alkyl, aryl and arylalkyl groups are optionally substituted, R15 in each occurrence is independently selected from H, C1-6 alkyl, R16 in each occurrence is independently selected from H, C1-6 alkyl and C6-10 arlo, wherein said alkyl and aryl groups are optionally substituted with 1 to 3 R20 groups; R17 and R18 in each occurrence are independently selected from H, C1-6 alkyl and C6-10 aryl or R17 and R18, together with the N to which they are attached, form a 3-7 membered heterocyclic ring ; wherein said alkyl and aryl groups, and heterocyclic ring are optionally substituted with 1 to 2 oxo groups; R20 in each occurrence is independently selected from F, Cl, Br, I, OR22, NR23R24, NHOH, No2, CN, CF3, C1-6 alkyl optionally substituted with 1 to 3 OH, C2-6 alkenyl, alkynyl C2-6, C3-7 cycloalkyl, 3-7 membered heterocycloalkyl, phenyl substituted by 0 to 1 OR25, 5 or 6 membered heteroaryl, arylalkyl, = O, C (= O) R22, CO2R22, OC (= O) R22 , C (= O) NR23R24, NR21C (= O) R2, NR21CO2R22, and OC (= O) NR23R24; R21 in each occurrence is independently selected from H and C1-6 alkyl; R22 in each occurrence is independently selected from H, C1-6 alkyl, C1-6-OH alkyl and C6-10 aryl; R23 and R24 in each occurrence are each independently selected from H, C1-6 alkyl and C6-10 aryl, or R23 and R24, together with the N to which they are attached, form a 3-7 membered heterocyclic ring optionally substituted with 1 to 3 oxo groups; R25 in each occurrence is independently selected from H, F, Cl, Br, C1-6 alkyl and C1-6 alkyloxy; x is 1, 2, 3 or 4; y is 0, 1 or 2; comprising the steps of: a) contacting a prochiral sulfide of the formula (2) wherein Ar, Y and R1 are as defined above, with a complex of metal chiral ligands, a base and an oxidizing agent in a organic solvent, and optionally b) isolate the sulfoxide obtained from the formula (1). Said method wherein the sulfoxide compound of formula (1) is obtained with an enantiomeric excess of at least 80%, 95% or 99%. Sulfoxide compound of the formula (1) selected from (-) or (+) - 2- [2- (4-chlorophenyl) benzyl] sulfinylacetamide; (-) or (+) - 2 - [([1,1'-biphenyl] -2-ylmethyl) sulfinyl] acetamide; and (-) or (+) - 2- [2- (3,4-dichlorophenoxy) -benzyl] sulfinylacetamide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05290560A EP1702915A1 (en) | 2005-03-14 | 2005-03-14 | Process for enantioselective synthesis of single enantiomers of thio-substituted arylmethanesulfinyl derivatives by asymmetric oxidation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR053167A1 true AR053167A1 (en) | 2007-04-25 |
Family
ID=34942003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP060100957A AR053167A1 (en) | 2005-03-14 | 2006-03-13 | PROCESS FOR THE ENANTIOSELECTIVE SYNTHESIS OF INDIVIDUAL ENANTIOMERS OF ARILMETANSULFINILO DERIVATIVES TIOSUSTITUTED BY ASYMMETRICAL OXIDATION |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US7893111B2 (en) |
| EP (2) | EP1702915A1 (en) |
| JP (2) | JP5192370B2 (en) |
| KR (1) | KR101256881B1 (en) |
| CN (1) | CN101142176B (en) |
| AR (1) | AR053167A1 (en) |
| AU (1) | AU2006224292B2 (en) |
| BR (1) | BRPI0607968A2 (en) |
| CA (1) | CA2599690C (en) |
| DK (1) | DK1863760T3 (en) |
| ES (1) | ES2392452T3 (en) |
| HK (1) | HK1105950A1 (en) |
| HR (1) | HRP20120939T1 (en) |
| IL (1) | IL185585A (en) |
| MX (1) | MX2007011159A (en) |
| MY (1) | MY157717A (en) |
| NO (1) | NO20074438L (en) |
| NZ (1) | NZ560986A (en) |
| SI (1) | SI1863760T1 (en) |
| TW (1) | TWI364412B (en) |
| WO (1) | WO2006097814A1 (en) |
| ZA (1) | ZA200707267B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ2009172A3 (en) * | 2009-03-17 | 2010-09-29 | Zentiva, K.S. | Process for preparing (S)-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole |
| CN104447440B (en) * | 2013-09-12 | 2016-05-18 | 中国科学院大连化学物理研究所 | A kind of method of catalysis asymmetric oxidation thioether |
| JP2022508648A (en) | 2018-10-05 | 2022-01-19 | アンナプルナ バイオ インコーポレイテッド | Compounds and compositions for treating conditions associated with APJ receptor activity |
| CN110746428A (en) * | 2019-10-29 | 2020-02-04 | 株洲千金药业股份有限公司 | Preparation method of R-type chiral sulfoxide compound |
| CN110698482A (en) * | 2019-10-29 | 2020-01-17 | 株洲千金药业股份有限公司 | Preparation method of S-type chiral sulfoxide compound |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4098824A (en) | 1975-10-02 | 1978-07-04 | Laboratoire L. Lafon | Benzhydrylsulphinyl derivatives |
| DE2708449C3 (en) | 1977-02-26 | 1981-01-08 | Hoechst Ag, 6000 Frankfurt | Process for the uniform dyeing of web-shaped textiles made of modified polyester fibers on tree dyeing machines |
| GB1584462A (en) | 1977-03-31 | 1981-02-11 | Lafon Labor | N-diaryl-malonamide and diarylmethyl-sulphinyl-acetamide derivatives and pharmaceutical compositions containing them |
| FR2593809B1 (en) * | 1986-01-31 | 1988-07-22 | Lafon Labor | BENZHYDRYLSULFINYLACETAMIDE, PROCESS FOR PREPARATION AND THERAPEUTIC USE |
| DE10224722C1 (en) | 2002-05-30 | 2003-08-14 | Leibniz Inst Fuer Festkoerper | High strength molded body used in the production of airplanes, vehicles spacecraft and implants in the medical industry is made from a titanium-based alloy |
| FR2849029B1 (en) | 2002-12-20 | 2005-03-18 | Lafon Labor | PROCESS FOR THE PREPARATION AND CRYSTALLINE FORMS OF OPTICAL ENANTIOMERS OF MODAFINIL. |
| EP1437345A1 (en) | 2003-01-13 | 2004-07-14 | Organisation de Synthese Mondiale Orsymonde | Novel method for preparing methyl 2-diphenylmethylsulfinylacetate |
| ATE442352T1 (en) | 2003-05-16 | 2009-09-15 | Cephalon France | METHOD FOR PRODUCING MODAFINIL |
| EP1516869A1 (en) | 2003-09-19 | 2005-03-23 | Cephalon France | Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation |
| US7368591B2 (en) | 2003-09-19 | 2008-05-06 | Cephalon France | Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation |
| EP1586560A1 (en) * | 2004-04-13 | 2005-10-19 | Cephalon, Inc. | Thio-substituted arylmethanesulfinyl derivatives |
| US7297817B2 (en) * | 2004-04-13 | 2007-11-20 | Cephalon France | Thio-substituted arylmethanesulfinyl derivatives |
| US7449481B2 (en) * | 2004-04-13 | 2008-11-11 | Cephalon, Inc. | Thio-substituted biaryl-methanesulfinyl derivatives |
| US20060086667A1 (en) | 2004-09-13 | 2006-04-27 | Cephalon, Inc., U.S. Corporation | Methods for the separation of enantiomeric sulfinylacetamides |
| EP1634861A1 (en) | 2004-09-13 | 2006-03-15 | Cephalon, Inc. | Methods for the separation of modafinil |
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2005
- 2005-03-14 EP EP05290560A patent/EP1702915A1/en not_active Withdrawn
-
2006
- 2006-03-13 AR ARP060100957A patent/AR053167A1/en not_active Application Discontinuation
- 2006-03-13 US US11/374,227 patent/US7893111B2/en not_active Expired - Fee Related
- 2006-03-14 WO PCT/IB2006/000552 patent/WO2006097814A1/en not_active Application Discontinuation
- 2006-03-14 NZ NZ560986A patent/NZ560986A/en not_active IP Right Cessation
- 2006-03-14 AU AU2006224292A patent/AU2006224292B2/en not_active Ceased
- 2006-03-14 BR BRPI0607968-7A patent/BRPI0607968A2/en not_active IP Right Cessation
- 2006-03-14 SI SI200631473T patent/SI1863760T1/en unknown
- 2006-03-14 EP EP06710540A patent/EP1863760B1/en active Active
- 2006-03-14 DK DK06710540.3T patent/DK1863760T3/en active
- 2006-03-14 MX MX2007011159A patent/MX2007011159A/en active IP Right Grant
- 2006-03-14 KR KR1020077023553A patent/KR101256881B1/en not_active IP Right Cessation
- 2006-03-14 ES ES06710540T patent/ES2392452T3/en active Active
- 2006-03-14 CA CA2599690A patent/CA2599690C/en not_active Expired - Fee Related
- 2006-03-14 TW TW095108615A patent/TWI364412B/en not_active IP Right Cessation
- 2006-03-14 CN CN2006800082077A patent/CN101142176B/en not_active Expired - Fee Related
- 2006-03-14 MY MYPI20061095A patent/MY157717A/en unknown
- 2006-03-14 JP JP2008501435A patent/JP5192370B2/en not_active Expired - Fee Related
-
2007
- 2007-08-28 ZA ZA200707267A patent/ZA200707267B/en unknown
- 2007-08-29 IL IL185585A patent/IL185585A/en not_active IP Right Cessation
- 2007-09-03 NO NO20074438A patent/NO20074438L/en not_active Application Discontinuation
- 2007-12-13 HK HK07113577.7A patent/HK1105950A1/en not_active IP Right Cessation
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2011
- 2011-01-04 US US12/984,279 patent/US8183294B2/en not_active Expired - Fee Related
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2012
- 2012-10-02 JP JP2012220208A patent/JP5698201B2/en not_active Expired - Fee Related
- 2012-11-19 HR HRP20120939TT patent/HRP20120939T1/en unknown
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